This study attempts to go beyond the individual-level factors that explain the underachievement of the Black male student and specifically focuses on the enormous growth of female-headed households. To this end, 2,849 middle school students in a large Midwestern school district in the United States were used. It was found that there is a significant association between the proportion of female-headed households and the achievement of Black male students only, in contrast to that of Black female and White students. Specifically, as the proportion of female-headed households in neighborhoods increases, Black male students tend to show poorer outcomes. Implications for the finding are reviewed.